Quinoline acylamino

The H mode of the pyrimidine ring construction assuming the stepwise formation of the N(l)-C(2) and C(2)-N(3) bonds as a result of the insertion of a component serving as the source of the C(2) atom is more often used in practice. The simplest modification involves intramolecular condensation of 3-(acylamino)thienopyri-dines produced by acylation of 3-amino-2-carbamoylthieno[2,3-Z>]pyridines or their structural analogs (1995PS83). An example is the synthesis of pyrimidothienobenzo-quinoline 98 from chloroacetamide 99. 

Quinolin 3-Amino-6-chlor-2,4-dihydroxy- E7a, 402 [4-COOR — 5-(2-acylamino — Ar) — 1,3-oxazol/HCl)... 

H-[Pg.874]

Oxazoles and 4,5-dihydrooxazoles can be transformed into quinolines. For instance, 5-(o-acylamino-aryl)oxazole-4-carboxylic esters 104, made from benzoxazinones 103 and isocyanoacetic ester, are converted into 3-aminO 4-hydroxy-2-quinolones 105 in an acid medium [109]. 

Thiophen Analogues of Quinoline.—Cyclization of (96) by treatment with AICI3 gave 4-amino-5-cyanothieno[2,3-/)]pyridines. 4-(Acylamino)thieno[2,3-f7]-pyridines were obtained from (186). 4-Amino-5-cyanothieno[2,3-Z>]pyridones were synthesized from 2-amino-3-cyanothiophens and ethyl cyanoacetate in the presence of sodium ethoxide. These compounds showed antibacterial activity. Through the reaction of 2-chloro-3-cyano-pyridines with ethyl thioglycollate followed by base-catalysed ring-closure, 3-aminothieno[2,3-6]pyridines were prepared, and these were transformed into various derivatives, including tricyclic systems. ... 

Benzol/] quinolines formation of, 150, 162 metal catalysts, action on, 189, 196 Benzol/i]quinoline, metal catalysts, action on, 189, 196 Benzoselenazole, 2-amino-, 68 Benzoselenazole-2-thione, 62 Benzoselenazol-2-one, 49 Benzo-1,2,4-thiadiazin-3-ones, methyla -tion of, 259 Benzothiazoles 2-acylamino-, 77... 

---